Pens might be the simplest example of attainable luxury. If you have a job (life?) that requires you write things down on paper then you should love the pen you use. Its such a tiny price to pay to upgrade something that you use constantly.
First step uni-ball Jetstream
Actually, you will probably want to find a pen that works best with your preferences. All I'm asking is that you go somewhere the sells a lot of pens, try enough of them to decide what you like, then pay a few bucks for the one that delights you. Uni-ball Jetstreams were the first pens to ever really make me happy so I agree with The Wirecutter's recommendation (although I like the cap tops as opposed to the clickable one pictured). They usually cost around $3, they feel good in the hand, and I love how they write. Thats it. Three bucks and you have a pen that is actually worth not losing.
Next step (deceased) Pilot Hi-Tec-C Cavalier
This density of this pen screams quality. Yes, the density. Don't care about the density of the pen you are using? That is because you haven't held a Pilot Hi-Tec-C Cavalier. It feels like rich people. I don't know why density makes things feel high quality, probably some backlash against cheap plastic products, but small heavy things are just delightful. You want this pen before even writing with it.
Pilot is phasing the Hi-Tec-C Cavalier out because the world is a cold dead place.
Of course, this can all turn into a slippery slope once you realize that using a nice pen can be nice in itself. While in Japan I stumble across Iroshizuku fountain pen ink and realized that I had been throwing my life away using black ink like a chump. So I ordered some cerulean blue ink I guess because in 2002 Oscar de la Renta did a line of cerulean gowns and I'm actually, rightly, terrified of creativity.
Then there is the Metropolitan, just click on that link and... hey, it is actually not that expensive! Not quite as dense as the Hi-Tec-C Cavalier, but it still looks, writes, and feels like a pen that should be in the hands of someone far richer and more successful than you (and certainly I) are. Fountain pens are more work than what you are probably used to so I can't unequivocally recommend them. But if you are already considering fountain pens then the Metropolitan is a great value.
The deep end TWSBI Diamond 580
It's just... I can't even talk about this pen without a post of its own. I admit it, I'm off the deep end here. All I can say is I live hard. I do my crosswords in pen.